Dichloromethane → 4-[9-(t-Butyldimethylsilyloxy)1-nonynyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

HRID 1859313Notes

Reaction equation

HRID 1859313 reaction equation
ClCCl.[Si:4]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]#[C:20][C:21]1(O)[C:30]2[C:25](=[CH:26][C:27]([O:31][CH3:32])=[CH:28][CH:29]=2)[S:24][CH2:23][C:22]1([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)[CH3:33])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5].C([BH3-])#N.[Na+]>[I-].[Zn+2].[I-].O>[Si:4]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]#[C:20][CH:21]1[C:30]2[C:25](=[CH:26][C:27]([O:31][CH3:32])=[CH:28][CH:29]=2)[S:24][CH2:23][C:22]1([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)[CH3:33])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:5])[CH3:6]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydrideHCID 220331564-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

Product 1

HCID 220334284-[9-(t-Butyldimethylsilyloxy)1-nonynyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochromanYield 62%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 962WaterSolvent

Procedure

Dichloromethane (30 ml) was added to 4-[9-(t-butyldimethylsilyloxy)-1-nonynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (946 mg, 1.66 mmol) obtained in Example 27, and then zinc iodide (795 mg, 2.49 mmol) and sodium cyanoborohydride (782 mg, 12.45 mmol) were added thereto. The reaction solution was stirred for 24 hours at room temperature and, after adding water, extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with column chromatography (n-hexane:ethyl acetate=9:1) to obtain 569 mg (yield: 62%, 3RS,4RS/3RS,4SR=5:1) of the title compound as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with column chromatography (n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-836c12995a8f4d74b036dfc1c7176c55
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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